Diisopropylamine → HCID 13057043, compound

HRID 1980053Notes

Reaction equation

HRID 1980053 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[O:13]=[C:14]1[NH:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1.[F:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=[O:33])=[CH:30][CH:29]=1>C1COCC1.O.CCCCCC>[O:13]=[C:14]1[NH:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:15]1[CH:32]([OH:33])[C:31]1[CH:34]=[CH:35][C:28]([F:27])=[CH:29][CH:30]=1

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 680234-FluorobenzaldehydeHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 13057043HCID 13057043, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of diisopropylamine (3.1 ml, 22 mmole) and dry THF (5 ml) at 0° C. under argon is added dropwise a hexane solution of n-butyllithium (13.8 ml, 22 mmole). After 3/4 hour, a solution of 2 (2.0 g, 10 mmole) in 75 ml of dry THF is added dropwise and stirred at 0° C. for 3 hours and 4-fluoro-benzaldehyde (13.6 g, 11 mmole) added dropwise. The reaction mixture was stirred at room temperature for 68 hours, poured into water, and extracted into ether. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure, and the residue recrystallized from ethanol to give 35. M.p. 219° C. (dec.).

Workup

  1. waitAfter 3/4 hour
  2. stirringThe reaction mixture was stirred at room temperature for 68 hours
  3. extractionextracted into ether
  4. washThe extract was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-e1d76c4eb6564a78af077f1cffa62328
Source dataset
uspto-grants-1984_11
Patent number
US04483988

Reaction notes

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